Testing winrm connectivity with command:
winrm id -r:hostname
Results in error message:
Error number: -2144108526 0x80338012 The client cannot connect to the destination specified in the request. Verify that the service on the destination is running and is accepting requests. Consult the logs and documentationfor the WS-Management service running on the destination, most commonly IIS or WinRM. If the destination is the WinRM service, run the following command on the destination to analyze andconfigure the WinRM service: "winrm quickconfig".
But wait!?! I did everything the error message told me to do. On my target machine there are no errors in the log and running the command “winrm qc” indicates that WinRM is already set up. So what is the problem?
winrm e winrm/config/listener
Listener [Source="GPO"] Address = * Transport = HTTP Port = 5985 Hostname Enabled = true URLPrefix = wsman CertificateThumbprint ListeningOn = null
Since I configured WinRM through Group Policy I decided to start there. Sure enough I had configured the policy “Allow automatic configuration of listeners” policy and set the IPv4 filter to be 192.168.1.1/24. After removing the filter and running gpudate on the target system, WinRM worked just like it was supposed to. Turns out the IPv4 filter value field does not understand subnet notation, instead you have to input a range such as 192.168.1.1-192.168.1.254. Lame.